This invention relates to compounds having hypoglycemic and/or growth promotant properties, said compounds being quaternary 7-substituted imidazo [2,1-b]-thiazolium and 9-substituted thiazolo[3,2-a]benzimidazolium salts.
Other than insulin, which is usually administered subcutaneously, the most useful oral medication employed in the treatment of diabetes are the sulfonylureas, many of which are currently being marketed. In addition, biguanides are also employed either alone or in combination with sulfonylureas in the treatment of this disease.
More recently, 1-substituted 3-(2-pyrimidinyl)imidazolium salts have been claimed in Belgium Pat. No. 743,510 and German patent application No. 1,964,282, to be active as hypoglycemic agents. Japanese patent application No. 7305899 reports the synthesis of pyridimium-pyrazine and their use as lowerers of blood sugar and free fatty acid levels. Wiegand, et al., J. Med. Chem., 15, 1326 (1972), review and report on the hypoglycemic activity of a number of azolylpyridinium salts.
Most commonly employed growth promotants are members of the anti-bacterial class of quinoxaline-di-N-oxides.
2,3,9-Trimethylbenzimidazo[2,1-b]thiazolium iodide has been prepared by de Stevens, et al., J. Am. Chem. Soc., 79, 5710 (1957), and imidazo[2,1-b]-thiazolium by Kondo, et al., J. Pharm. Soc., Japan, 57, 1050 (1937) (C.A. 32, 3398 (1938) and Kickhofen, et al., Chem. Ber., 88, 1109 (1955) (C.A. 50, 13911 (1956).